Photo by David Cedrone

Dorchester holiday homes

We found 1,324 holiday rentals — enter your dates for availability

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August 2025

September 2025

Discover a selection of 33 homes, 71 apartments and other holiday rentals in Dorchester that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday homes have the best amenities for hanging out with the people that matter most, which might include a garden and Wi-Fi. What you'll find is a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Dorchester

Showing deals for:21 Nov - 28 Nov

Exceptional

(78 reviews)

Beautiful Boston Brownstone!

Boston, MA

8% off

NZ$978 per night

includes taxes & fees

Wonderful

(9 reviews)

Luxury apartment seaport

Boston, MA

8% off

NZ$824 per night

includes taxes & fees

Very good

(6 reviews)

Back-Bay 2BR Penthouse w Roof top and GYM

Boston, MA

15% off

NZ$978 per night

includes taxes & fees

Wonderful

(5 reviews)

Luxurious apartment in Fenway

Boston, MA

8% off

NZ$1,022 per night

includes taxes & fees

Exceptional

(32 reviews)

Elegant Back Bay Brownstone - Comm Ave - 1+ Bed - One Week Minimum

Boston, MA

8% off

NZ$747 per night

includes taxes & fees

You will love gathering and eat in this space featuring a stunning wall art,Tv.

Very good

(6 reviews)

Great for large group mins from DowntownBostonFenway Convention Grill Free Prkg

Boston, MA

8% off

NZ$1,493 per night

includes taxes & fees

Exceptional

(169 reviews)

Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi

Boston, MA

8% off

NZ$826 per night

includes taxes & fees

Exceptional

(10 reviews)

Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH

Boston, MA

8% off

NZ$1,504 per night

includes taxes & fees

Exceptional

(7 reviews)

76/1 - SPRING GETAWAY 10% OFF! Spacious 4-bedroom apartment in charming Boston

Boston, MA

12% off

NZ$916 per night

includes taxes & fees

Exceptional

(43 reviews)

* Beautiful condo 1st floor walk to public trans T mins to downtown Boston

Boston, MA

9% off

NZ$1,181 per night

includes taxes & fees

Excellent

(154 reviews)

Historic Beacon Hill Duplex -2 bed 1.5 bathrooms Condo -heart of Boston

Boston, MA

6% off

NZ$645 per night

includes taxes & fees

Very good

(15 reviews)

Brand-new spacious 4 bedroom home, minutes from train station, free st parking

Boston, MA

8% off

NZ$984 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Find properties near top attractions in Dorchester

John F. Kennedy Presidential Library and Museum

Find the best place to stay - Dorchester

Spacious, New Renovation | Near T

Sleeps 18 · 6 bedrooms · 3+ bathrooms

14a-Cozy and well decorated apartment in awesome Boston

Sleeps 13 · 3 bedrooms · 1+ bathroom

Global Luxury Suites Downtown Boston

Sleeps 3 · 1 bedroom

14b-Charming, beautiful 3-bedroom apartment in Boston

Sleeps 12 · 3 bedrooms · 1+ bathroom

30/1 - SPRING GETAWAY 10% OFF! Fully furnished 1st floor apartment in Boston

Sleeps 12 · 4 bedrooms · 1 bathroom

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday home accommodation in Dorchester?

The most sought-after types of holiday homes in Dorchester are apartments. Prefer something different? Bookabach has many options to match our guests' requirements, so you'll see holiday homes in loads of shapes and sizes. The ideal home away from home is waiting for you — book yours today.

How much does it cost to rent a holiday home in Dorchester?

The average price for a holiday home in Dorchester is determined by several factors, including property type, length of stay and time of year. Whether you're thinking about a sprawling villa with space for extended family or a cosy condo perfect for just you and the kids, just enter your travel dates to view stays with terrific value.

How much does it cost to rent a beach house in Dorchester?

When you travel and the style and size of the property will influence how much you'll pay for your beachside stay. Click on your Dorchester travel dates to see all your options on Bookabach. Did someone just say "private pool"? Use the filters to select the features and amenities you need.

Are there pet-friendly holiday homes in Dorchester?

Pack a travel bag and a bone for your puppy dog because Dorchester has 47 holiday homes that put out the welcome mat to pets. Let your happy hound have fun with the family at one of our pet-friendly holiday homes on Bookabach. Simply enter your dates and destination, then check the "Pets allowed" filter box.

Can I rent a house with a pool in Dorchester?

Add a whole new level of fun to your trip by booking one of the five houses with a private pool in Dorchester. Use our search filter to find properties with pools on Bookabach, then spend carefree days splish-splashing around in a swimming pool that's just for you.

What are popular home amenities in Dorchester?

When it comes to home amenities that guests are looking for in Dorchester, nearby museums, a swimming pool and a nearby waterfront are the most popular. With Bookabach holiday homes, you'll enjoy choices to suit your taste and style, whether you're on a trip with family members, friends or even pets.

Are there large group holiday homes in Dorchester?

With eight properties that can host 10 or more guests in Dorchester, you won't have to cross anyone off the invite list. From extended family holidays to events like Christmas and birthday parties, Bookabach will help you find a large group home that fits the occasion.

Are there holiday homes in Dorchester that welcome kids?

Bring the whole group together for fun-filled adventures in Dorchester at one of our 46 family-friendly holiday homes. These stays come with conveniences that are just perfect for getaways with the little ones, including full kitchens, extra bedrooms and entertainment units. Simply click on the "Properties good for families" filter box and pick out your favourite.

What are the top attractions for families in Dorchester?

Keeping the kids entertained during your stay in Dorchester is simple with these family-friendly attractions:

New England Aquarium
Museum of Science
Boston Tea Party Ship

Are there one-bedroom holiday homes in Dorchester?

You'll find 16 one-bedroom properties in Dorchester to choose from. A one-bedroom holiday home is an excellent option if it's only two of you or if you're travelling on your own. Throw in more convenience, space and privacy compared to a hotel, and you're sure to have an unforgettable getaway.

Can I find two-bedroom holiday homes in Dorchester?

Dorchester has 11 two-bedroom holiday properties that you can choose from. Book a holiday home with all the comfort and privacy you want at a price that's hard to resist on Bookabach.

Are there holiday homes with WiFi in Dorchester?

Whether you'd like to stay in touch with the news, make a video call or update your social media, there are 13 holiday homes with WiFi in Dorchester. Check the "WiFi" box when searching on Bookabach and stay connected on your holiday.

How can I find holiday homes with air conditioning in Dorchester?

Decide on your travel dates and then use the filters to view holiday homes with air conditioning in Dorchester on Bookabach. With 44 air-conditioned properties available here, you can enjoy a cool and comfortable trip.

How old do you have to be to rent a holiday home in Dorchester?

The minimum age requirements can differ between properties on Bookabach, so check the rules of the holiday home in Dorchester you want to book. But in general, it's 16, 18 or 21.

How long can I rent a holiday home in Dorchester for?

The amount of time you can stay in a Dorchester holiday home for depends on the property. Just enter your travel dates to find options offering extended stays. They feature the things you need to make your extended getaway more comfortable and convenient, such as kitchens and air conditioning. Some Bookabach holiday homes may also offer discounted weekly or monthly prices, so you can have a longer stay for less.